Toluene → Ethyl orthoformate

HRID 979629Notes

Reaction equation

HRID 979629 reaction equation
O[CH2:2][CH2:3][O:4][C:5](=[O:17])CCCCCCCCC([O-])=O.CN1C(C)(C)C[CH:22]([OH:27])[CH2:21]C1(C)C.[C:30]1(C)C=CC=C[CH:31]=1>C1(C)C(S(O)(=O)=O)=CC=CC=1.O>[CH:5]([O:4][CH2:3][CH3:2])([O:17][CH2:30][CH3:31])[O:27][CH2:22][CH3:21]

Participants

6

Reactant 3

HCID 1140TolueneHCID 754724-Piperidinol, 1,2,2,6,6-pentamethyl-HCID 21889638HCID 21889638, compound

Product 1

HCID 31214Ethyl orthoformate

Reagents, catalysts & solvents 2

HCID 69252-Methylbenzenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

Mono(2-hydroxyethyl)sebacate and 23.6 g (0.1 mole) 1,2,2,6,6-pentamethylpiperidin-4-ol 17.1 g (0.1 mole) were esterified by heating with 0.4 g toluenesulfonic acid catalyst and 100 cc toluene in a reflux apparatus including a Dean-Stark trap to collect the reaction water as it evolved. When no more water obtained 22.2 g (0.15 mole) triethyl orthoformate was added and heating under reflux continued for 9 hours. Stripping under vacuum removed toluene and excess triethyl orthoformate, and left an oily liquid product represented by formula ##STR49##

Workup

  1. customto collect
  2. customthe reaction water as it

Sources & evidence

ORD record
ord-61b719d0960f424a97748a758cfbdd72
Source dataset
uspto-grants-1987_05
Patent number
US04668722

Reaction notes

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